This invention is concerned with a microbial process for the production of compositions of matter containing octalactone having the generic structure: ##STR6##
Considerable time and effort have been expended by microbiologists in the search for better processes for the production of saturated lactones; and more generally, lactones per se. U.S. Pat. No. 3,076,750 discloses a method for preparing certain optically active lactones and the corresponding hydroxycarboxylic acids by microbial reduction of ketocarboxylic acids. The metabolism of ricinoleic acid by some Candida strains was investigated by Okui, et al (J. Biochemistry, 54,536-540, 1963) who showed that gamma hydroxy decanoic acid was an intermediate in the oxidative degradation of ricinoleic acid. However, only trace amounts of gamma hydroxydecanoic acid were recovered from the fermentation medium due to the metabolysis of gamma hydroxydecanoic acid upon completion of the fermentation, and the toxicity of ricinoleic acid to the microorganism, which limits the amount of substrate that can be used.
U.S. Pat. No. 4,560,656 provided a method of producing optically active gamma hydroxydecanoic acid comprising culturing or incubating a microorganism capable of hydrolyzing castor oil, and effecting beta-oxidation of the resulting hydrolysate in the presence of castor oil, to produce gamma hydroxydecanoic acid.
U.S. Pat. No. 4,560,656 also provided a method of producing optically active gamma hydroxydecanoic acid comprising enzymatically hydrolyzing castor oil using lipase to form an enzymatic hydrolysate and culturing or incubating a microorganism capable of effecting beta-oxidation of the enzymatic hydrolysate in the presence of said hydrolysate to produce gamma hydroxydecanoic acid.
U.S. Pat. No. 4,560,656 also provided a method of producing optically active gamma hydroxydecanoic acid comprising culturing or incubating a microorganism capable of hydrolyzing castor oil and a microorganism capable of effecting beta-oxidation of castor oil hydrolysate in the presence of castor oil to produce gamma hydroxydecanoic acid.
European Published Patent Application 258993 published on Apr. 9, 1988 discloses a process for the production of optically active gamma hydroxydecanoic acid suitable for conversion to optically active gamma decalactone. The process covers steps of:
(a) culturing sporobolomyces odorous; and/or rhodotorula glutinis on a medium containing a ricinoleic acid sources at 15.degree.-35.degree. C. at a pH of 3-9 and, optionally; PA0 (b) lactonizing the resulting gamma hydroxydecanoic acid to gamma decalactone. PA0 Candida petrophilum, ATCC 20226; PA0 Candida oleophila, ATCC 20177; PA0 Candida sp., ATCC 20504; and PA0 Candida sake, ATCC 28137
Lion Corporation, European Published Patent Application No. 269,351 filed on Nov. 17, 1987 discloses a method for producing a fat containing gamma linolenic acid comprising the steps of culturing a microorganism belonging to the genus Absidia, the genus Mortierella, the genus Mucor, the genus Rhizopus or the genus Syncephalastrum with a fatty acid or an ester thereof as the carbon source, and converting the fatty acid or the ester thereof to gamma linolenic acid. The microorganisms exemplified are Absidia corymbifera, IFO 4010, Mortierella isabellina, IFO 7873, Rhizopus oryzae, IFO 5418 and Syncephalastrum racemosum, IFO 4816. Fatty acids or esters exemplified are set forth in paragraph 5, on page 3 of European Application 269,351, to wit, fatty acids having 8 to 22 carbon atoms, particularly 8 to 18 carbon atoms, as exemplified by n-capric acid, n-caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid and linoleic acid.
PCT Application 89/12104 (BASF Corporation) discloses a process for the preparation of gamma and delta lactones from organic carboxylic acids or derivatives thereof by means of cultivating, under aerobic conditions, a fungus of the genus Mucor in a suitable medium containing the carboxylic acid or a derivative thereof. Examples of the Mucor fungus are the following strains: M. subtillissimus, M. mucedo, M. miehei, M. circinelloides, M. luteus, M. flavus, M. corticolus and M. albo-ater. Furthermore, Example 2 of PCT Application No. 89/12104 indicates that when using Mucor circinelloides and using an ethyl octanoate substrate, the resulting product recovered is 49.4% gamma octalactone having the structure: ##STR7## having a specific rotation (alpha.sub.d of -39.8).
Kutney, et al, Helvetica Chimica Acta., Volume 65, Pasc. 5 (1982) No. 127, at pages 1343-1350, discloses the use of Mortierella isabellina in carrying out a gamma hydroxylation of the compound having the structure: ##STR8## to form the compound having the structure: ##STR9## according to the reaction:
U.S. Pat. No. 4,960,597 issued on Oct. 2, 1990 described a process for the preparation of compositions of matter containing both saturated and unsaturated lactones including the saturated gamma decalactone. Thus, U.S. Pat. No. 4,960,597 described a process for the preparation of compositions of matter defined according to the generic structure: ##STR10## wherein R represents C.sub.6 alkyl or alkenyl, and X represents C.sub.2, C.sub.4 or C.sub.6 alkylene or alkylene; with the proviso that R is C.sub.6 alkyl when X is alkenylene and R is C.sub.6 alkenyl when X is alkenylene by means of the sequential steps of (i) fermentation of castor oil or ricinoleic acid using a microorganism selected from the group consisting of:
whereby gamma hydroxydecanoic acid and a mixture of other acids defined according to the generic structure: ##STR11## is formed wherein Y represents an oxo-saturated, oxo-unsaturated or di-unsaturated C.sub.9, C.sub.11 or C.sub.13 moiety according to the reaction: ##STR12## (ii) lactonization of the resulting gamma hydroxydecanoic acid by means of simultaneous acidification and heating according to the reaction: ##STR13## and (iii) lactonization (via distillation) of one or more of the resulting acids defined according to the structure: ##STR14## according to the reaction: ##STR15## wherein the sum of the number of carbon atoms in the X moiety and in the R moiety is equal to the number of carbon atoms in the Y moiety minus 1.
In the flavor and fragrance art, a need has arisen for the development and efficient production of naturally occurring lactones which have heretofore been found to be useful and necessary in the creation of flavor formulations used in augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos and smoking tobaccos and also useful in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles, hair preparations, cosmetic powders and the like).
Gamma octalactone defined according to the structure: ##STR16## particularly its optical isomers having the structures: ##STR17## is useful particularly for forming butter flavors for use in flavoring products which cannot contain any natural butter due to health reasons. Thus, compounds having the structures: ##STR18## are found to be highly useful in producing butter flavored margarine. Furthermore, the combination of the compounds having the structures: ##STR19## taken further together with other naturally occurring materials produced via fermentation including but not limited to, for example, the compounds having the structures: ##STR20## has been found to be highly useful in the production of butter flavors as well as in the production of perfumery materials, colognes and perfumed articles.
Nothing in the prior art however discloses the ability by means of fermentation to create novel mixtures of lactones together with other furan derivatives for use in augmenting or enhancing the organoleptic properties of consumable materials.